EP0627912B1 - Gels for encapsulation of biological materials - Google Patents
Gels for encapsulation of biological materials Download PDFInfo
- Publication number
- EP0627912B1 EP0627912B1 EP93907078A EP93907078A EP0627912B1 EP 0627912 B1 EP0627912 B1 EP 0627912B1 EP 93907078 A EP93907078 A EP 93907078A EP 93907078 A EP93907078 A EP 93907078A EP 0627912 B1 EP0627912 B1 EP 0627912B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- macromer
- polymerization
- cells
- peg
- biological material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Abstract
Description
This results in much enhanced stability over that of the previous approach and in the enhancement of biological responses to these materials. The penetrant may be chemically modified to be a prepolymer macromer, i.e. capable of being polymerized itself. This polymerization can be initiated thermally or by exposure to visible, ultraviolet, infrared, gamma ray, or electron beam irradiation, or to plasma conditions. In the case of the relatively nonspecific gamma ray or electron beam radiation reaction, chemical incorporation of particularly reactive sites may not be necessary.
Function of Encapsulated Islet Cells SGS Glucose Concentration (mg%) | |||
Initial | Subsequent | ||
60 | 300 | 60 | |
Insulin/Islet/hr (µU/ml) | |||
Diffusion Overcoat Method | 1.0 | 10.04±3.56 | 2.54±0.76 |
Mineral Oil Overcoat Method | 1.0 | 10.23±3.28 | 1.02±0.78 |
Free Islet Control | 1.0 | 3.74±1.4 | 1.9±0.17 |
Secretion of Insulin from Islet Cells Islet Insulin Secretion | |||
Glucose Concentration (mg%) | |||
60 | 300 | 60 | |
Insulin/islet/hr (µU/ml) | |||
Free islets | 1.0 | 3.74 ± 1.40 | 1.9 ± 0.17 |
Encapsulated Islets | 1.0 | 20.81 ± 9.36 | 2.0 ± 0.76 |
Microsphere Coverage with Cell Overgrowth Following Implantation Intraperitoneally for 4 Days. | |
Composition of PEG gel | % Cell coverage |
18.5K | <1 |
18.5k 90%: 0.4 | <1 |
18.5k 50%: 0.4k 50% | <1 |
35k 90%: 0.4 | 5-7 |
35k 50%: 0.4k 50% | <1 |
Alginate-poly(L-lysine) | 60-80 |
Gelling Times of Irradiated Polymer | |
Polymer Size | Gel Time (sec) |
(mean ± S.D.) | |
0.4K | 6.9±0.5 |
1K | 21.3±2.4 |
6K | 14.2±0.5 |
10K | 8.3±0.2 |
18.5K | 6.9±0.1 |
20K | 9.0±0.4 |
Extent of Cellular Overgrowth on Gels PEG Diacrylate for Gels Extent of Cellular Overgrowth (mol wt, Daltons) | |
400 | 5-10% |
1,000 | 15-25% |
5,000 | 3-5% |
6,000 | 2-15% |
10,000 | 10-20% |
18,500 | 4-10% |
Gel Strength Tests | ||||
PEG Acrylate Precursor Molecular Weight | ||||
0.4K | 6K | 10K | 18.5K | |
Stress (kPa) | 168+/-51 | 98+/-15 | 33+/-7 | 115+/-56 |
| 8+/-3 | 71+/-13 | 110+/-9 | 40+/-15 |
Slope | 22+/-5 | 1.32+/-0.31 | 0.27+/-0.04 | 2.67+/-0.55 |
The discs were weighed (W1) and then extracted repeatedly with chloroform for 1 day. The discs were dried again and weighed (W2). The gel fraction was calculated as W2/W1. This data appears in Table 7.
Data for gel water contents. | ||
Polymer Code | % Total Water | % Gel Content |
0.4 | - | 99.8±1.9 |
1K | 79.8±2.1 | 94.5±2.0 |
6k | 95.2±2.5 | 69.4±0.6 |
10k | 91.4±1.6 | 96.9±1.5 |
18.5k | 91.4±0.9 | 80.3±0.9 |
20k | 94.4±0.6 | 85.0±0.4 |
Resistance to degradation of Polymer Implants | ||
TIME IMPLANTED | STRESS (KPa) (mean±error) | STRAIN AVE. (mean±error) |
1 WK | 52.8±16.7 | 0.32±0.19 |
3 WK | 36.7±10.6 | 0.37±0.17 |
6 WK | 73.3±34.9 | 0.42±0.26 |
8 WK | 34.1 | 0.30# |
CONTROL | 44.9±5.3 | 0.22±0.22 |
Calcification data on PEG-tetraacrylate (mol. wt. 18.5K) gel implants | |
TIME (Days) | CALCIFICATION (mean±error) (mg Calcium/g of Dry gel wt.) |
7 | 2.33 ± 0.20 |
21 | 0.88 ± 0.009 |
42 | 1.08 ± 0.30 |
56 | 1.17 ± 0.26 |
Hemoglobin at the desired amount | |
PEG DA (MW 10000) | 35% |
PEG DA (MW 1000) | 5 |
PBS | |
60% |
Immunogenicity of these enzymes prevents direct use for chemotherapy. Entrapment of such enzymes in PEG gels, however, can support successful chemotherapy. A suitable formulation can be developed for either slow release or no release of the enzyme.
Catalase at the desired amount | |
PEG DA (MW 10000) | 35% |
PEG DA (MW 1000) | 5 |
PBS | |
60% |
Survival of infected cells indicates successful action of the drug. Lack of biocompatibility is a documented problem in this approach to drug evaluations, but can be overcome by using the gels described herein.
Claims (34)
- A non-cytotoxic method for encapsulating, sealing, plugging, or supporting a biological material or for preparing a biocompatible substrate, the method comprising:a) providing a macromer mixture by mixing(i) a synthetic polymeric water soluble biocompatible macromer comprising at least two free radical-polymerizable substituents, wherein the macromer is non-toxic and has a molecular weight of at least 400; and(ii) a non-toxic free radical polymerization initiator selected from a visible light or a long wavelength ultraviolet light-activatable free radical initiator;b) coating a biological material or a substrate in vitro with the macromer mixture, wherein the biological material is selected from the group consisting of mammalian cells, sub-cellular organelles, sub-cellular components, and aggregates of mammalian cells and the substrate is selected from microcapsules, woven matrices, porous matrices and prosthetic implants; andc) exposing the coated biological material or coated substrate to visible or long wavelength ultraviolet light to cause polymerization of the macromers, thereby forming a polymeric gel with a degree of polymerization greater than 10.
- A non-cytotoxic method for encapsulating, sealing, plugging, or supporting a biological material, the method comprising:a) contacting a biological material with a solution of a non-toxic free-radial polymerization initiator selected from the group consisting of visible or long wavelength ultraviolet light-activatable initiators, to allow binding of the initiator to the biological material;b) removing the unbound initiator by washing or dilution;c) contacting the biological material in vitro with a water-soluble non-toxic biocompatible macromer comprising at least two free-radical polymerizable substituents, the macromer having a molecular weight of at least 400; andd) exposing the biological material to an agent activating said initiator to cause polymerization of the macromers, thereby forming a polymeric gel with a degree of polymerization greater than 10.
- The method of Claim 2 wherein the biological material is selected from the group consisting of mammalian cells, sub-cellular organelles, sub-cellwlar components and aggregates of mammalian cells.
- The method of Claim 1 or 2 wherein the free-radical polymerizable substituents contain carbon-carbon double or triple bonds.
- The method of Claim 1 or 2 wherein the initiator is used together with a non-toxic catalyst.
- The method of any preceding claim wherein the water soluble macromer is selected from the group consisting of poly(ethylene glycol), poly(ethylene oxide), poly(vinyl alcohol), poly(vinylpyrrolidone), poly(ethyloxazoline), or a block or random copolymer thereof comprising two or more free-radical polymerizable substituents.
- The method of Claim 2 wherein the water soluble macromer is selected from the group consisting of poly (amino acids), polysaccharides, proteins or a block or random copolymer thereof comprising two or more free-radical polymerisable substituents.
- The method of Claim 7 wherein the polysaccharide is selected from the group consisting of alginate, hyaluronic acid, chondroitin sulfate, dextran, dextran sulfate, heparin, heparin sulfate, heparan sulfate, chitosan, gellan gum, xanthan gum, guar gum and k-carrageenan.
- The method of Claim 7 wherein the protein is selected from the group consisting of gelatin, collagen, albumin, zein and elastin.
- The method of any preceding claim wherein the gel is prepared from macromers comprising an acrylate terminated poly(ethylene glycol).
- The method of Claim 1 or 2 for encapsulating a biologically active molecule wherein the biologically active molecule is selected from the group consisting of peptides, proteins, polysaccharides, nucleic acids, organic drugs, and inorganic drugs.
- The method of Claim 1 or 2 wherein the polymerization initiator is selected from the group consisting of an eosin dye, a substituted eosin dye, eosin Y, ethyl eosin, riboflavin, acetophenone, a substituted acetophenone, a fluorescein dye, a substituted fluorescein dye, camphorquinone, rose bengal, methylene green, methylene blue, acridine orange, erythrosin, phloximine, thionine, xanthine dyes, and thioxanthine dyes.
- The method of Claim 5 wherein the catalyst is an amine.
- The method of Claim 13 wherein the amine is selected from the group consisting of triethanolamine, triethylamine, ethanolamine, N-methyl diethanolamine, N,N-dimethyl benzylamine, dibenzyl amine, N-benzyl ethanolamine, N-isopropyl benzylamine, tetramethyl ethylene-diamine, lysine, ornithine, histidine and arginine.
- The method of Claim 1 or 2 wherein polymerization is initiated by light having a wavelength of between 320 nm and 800 nm.
- The method of Claim 15 wherein the light has a wavelength of 514 nm or 365 nm.
- The method of Claim 3 wherein the unbound initiator is removed by dilution with the macromer solution such that polymerization occurs only at the surface of the mammalian cell, sub-cellular organelle, sub-cellular component or the mammalian cell aggregate.
- The method of Claim 1, wherein the macromer solution is shaped and then polymerized.
- The method of Claim 1, wherein the gel contains a supporting structure.
- The method of Claim 1 wherein the polymer is selected and the polymerization is controlled to produce a desired permeability around the encapsulated biological material or biocompatible substrate.
- The method of Claim 1 wherein the macromer is coated on the surface of a three-dimensioned object and the coated surface is irradiated with light to initiate macromer polymerisation.
- The method of Claim 1, wherein a photopolymerizable polycation is pre-adsorbed to the biological material or substrate being encapsulated to increase attachment of the gel to the biological material or substrate.
- The method of Claim 1 or 2 wherein the biological material is selected from primary or established lines of mammalian cells, sub-cellular organelles, and sub-cellular non-organelle components.
- The method of Claim 23 wherein the cell line is selected from pancreatic islet cells, human foreskin fibroblasts, Chinese hamster ovary cells, beta cell insulomas, lymphoblastic leukemia cells, mouse 3T3 fibroblasts, dopamine secreting ventral mesencephalon cells, neuroblastoid cells, adrenal medulla cells and T-cells.
- The method of Claim 1 wherein the biological material is first encapsulated in a microcapsule.
- The method of Claim 25 wherein the microcapsule is comprised of ionically coagulatable or thermally coagulatable polymers which are non-toxic to the encapsulated material.
- The method of Claim 1 wherein the macromer solution further comprises an accelerator to accelerate the rate of polymerization.
- The method of Claim 27 wherein the accelerator comprises a small molecule containing an allyl, vinyl or acrylate group.
- The method of Claim 28 wherein the accelerator is selected from the group consisting of N-vinyl pyrrolidinone, 2-vinyl pyridine, 1-vinyl imidazole, 9-vinyl carbazole, acrylic acid and 2-allyl, 2-methyl, 20 1-3-cyclopentane dione.
- The method of Claim 1 wherein the macromer mixture is an aqueous solution.
- A biological material or a biocompatible substrate obtainable by a method of Claim 1 or a biological material obtainable by a method of Claim 2 for use in medicine.
- Use of a biological material or a biocompatible substrate obtainable by a method of Claim 1 or a biological material obtainable by a method of Claim 2 in the preparation of a medicament for use in the treatment of metabolic defects or diseases.
- Use of a macromer mixture as claimed in anyone of Claims 1, 2, 4 to 16, 18 to 20, 22 and 27 to 30 in the manufacture of a medicament for the treatment of metabolic defects or diseases.
- Use of a macromer mixture as claimed in any one of Claims 1, 2, 4 to 16, 18 to 20, 22 or 27 to 30 in the manufacture of a medicament for use as adhesives, as tissue supports or as plugs, or as barriers to present the interaction of one cell tissue with another cell or tissue.
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
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US84348592A | 1992-02-28 | 1992-02-28 | |
US843485 | 1992-02-28 | ||
US87054092A | 1992-04-20 | 1992-04-20 | |
US870540 | 1992-04-20 | ||
US07/958,870 US5529914A (en) | 1990-10-15 | 1992-10-07 | Gels for encapsulation of biological materials |
US958870 | 1992-10-07 | ||
PCT/US1993/001776 WO1993016687A1 (en) | 1992-02-28 | 1993-03-01 | Gels for encapsulation of biological materials |
Publications (3)
Publication Number | Publication Date |
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EP0627912A1 EP0627912A1 (en) | 1994-12-14 |
EP0627912A4 EP0627912A4 (en) | 1995-07-26 |
EP0627912B1 true EP0627912B1 (en) | 2004-05-12 |
Family
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP93907078A Expired - Lifetime EP0627912B1 (en) | 1992-02-28 | 1993-03-01 | Gels for encapsulation of biological materials |
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US (4) | US5529914A (en) |
EP (1) | EP0627912B1 (en) |
JP (1) | JP3011767B2 (en) |
KR (1) | KR100323043B1 (en) |
AT (1) | ATE266389T1 (en) |
AU (1) | AU683209B2 (en) |
BR (1) | BR9306041A (en) |
CA (1) | CA2117584C (en) |
DE (1) | DE69333512T2 (en) |
DK (1) | DK0627912T3 (en) |
ES (1) | ES2220906T3 (en) |
NZ (1) | NZ251039A (en) |
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WO1994015589A1 (en) * | 1992-12-30 | 1994-07-21 | Clover Consolidated, Limited | Cytoprotective, biocompatible, retrievable macrocapsule containment systems for biologically active materials |
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-
1992
- 1992-10-07 US US07/958,870 patent/US5529914A/en not_active Expired - Lifetime
-
1993
- 1993-03-01 BR BR9306041A patent/BR9306041A/en not_active Application Discontinuation
- 1993-03-01 CA CA002117584A patent/CA2117584C/en not_active Expired - Lifetime
- 1993-03-01 DK DK93907078T patent/DK0627912T3/en active
- 1993-03-01 WO PCT/US1993/001776 patent/WO1993016687A1/en active IP Right Grant
- 1993-03-01 EP EP93907078A patent/EP0627912B1/en not_active Expired - Lifetime
- 1993-03-01 NZ NZ251039A patent/NZ251039A/en unknown
- 1993-03-01 AU AU37809/93A patent/AU683209B2/en not_active Expired
- 1993-03-01 JP JP5515100A patent/JP3011767B2/en not_active Expired - Lifetime
- 1993-03-01 DE DE69333512T patent/DE69333512T2/en not_active Expired - Lifetime
- 1993-03-01 PT PT93907078T patent/PT627912E/en unknown
- 1993-03-01 ES ES93907078T patent/ES2220906T3/en not_active Expired - Lifetime
- 1993-03-01 AT AT93907078T patent/ATE266389T1/en active
-
1994
- 1994-08-29 KR KR1019940703035A patent/KR100323043B1/en not_active IP Right Cessation
-
1995
- 1995-06-07 US US08/480,678 patent/US5801033A/en not_active Expired - Lifetime
-
1997
- 1997-01-13 US US08/783,387 patent/US6258870B1/en not_active Expired - Fee Related
-
2001
- 2001-03-19 US US09/811,901 patent/US6911227B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
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US6911227B2 (en) | 2005-06-28 |
DE69333512D1 (en) | 2004-06-17 |
DE69333512T2 (en) | 2005-05-12 |
AU3780993A (en) | 1993-09-13 |
US6258870B1 (en) | 2001-07-10 |
WO1993016687A1 (en) | 1993-09-02 |
NZ251039A (en) | 1996-03-26 |
US20020058318A1 (en) | 2002-05-16 |
JPH07506961A (en) | 1995-08-03 |
DK0627912T3 (en) | 2004-06-28 |
US5801033A (en) | 1998-09-01 |
BR9306041A (en) | 1997-11-18 |
KR100323043B1 (en) | 2002-07-27 |
EP0627912A4 (en) | 1995-07-26 |
EP0627912A1 (en) | 1994-12-14 |
JP3011767B2 (en) | 2000-02-21 |
PT627912E (en) | 2004-08-31 |
CA2117584A1 (en) | 1993-09-02 |
ATE266389T1 (en) | 2004-05-15 |
CA2117584C (en) | 1998-09-22 |
AU683209B2 (en) | 1997-11-06 |
US5529914A (en) | 1996-06-25 |
KR950700054A (en) | 1995-01-16 |
ES2220906T3 (en) | 2004-12-16 |
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